Broken Boulevards
by FirefliesAndLight
Summary: Looking for extra some cash, and just wanting a way out of her play-it-safe life, Olivia Maxwell takes up a position in helping Lester Crest and the boys pull off their schemes and heists. Almost too soon, Olivia is pulled into the whirlwind of living in crime, in Los Santos, the "bleeding city".
1. Chapter One - O

**Note, Summary, and, Disclaimer**

**I really enjoy this series of games, and realize that there aren't a lot of fics in this category. I don't care. I'm writing this anyways and hopefully you enjoy. I haven't finished the actual game yet, so I can't say what time frame this story takes place. Don't forget to review, comment and most of all enjoy. Rated M for language and future violence and sexual content – You've been warned.**

**_P.S._**** Please don't flame. I'd really appreciate it. - J**

**Summary:**** Looking for extra some cash, and just wanting a way out of her play-it-safe life, Olivia Maxwell takes up a position in helping Lester Crest and the boys pull off their schemes and heists. Almost too soon, Olivia is pulled into the whirlwind of living in crime, in Los Santos, the "bleeding city". Story will have romance, crime, drama, sexual content, language and violence.**

**Disclaimer:**** As much as I would love to, I sadly, do not own the Grand Theft Auto franchise, or, any of the characters. I do, however, own my OC, Olivia, and any other OC's thrown into the story, along with the story line itself. **

**Chapter One**

**_O_**

Michael De Santa was just walking into his front door, when his phone began to ring. He pulled it from his pocket and looked down at the caller ID. Lester. He rolled his eyes, pressing the talk button. "Hello."

Lester's snivelling voce immediately filled his ear. "Michael."

Michael rolled his eyes again, shutting the door behind him. "It's who you called, Lest."

"Good, good." Lester crackled. "Listen, Michael. You home yet?"

"Just got in." Michael answered, throwing his coat on his couch as if to silently prove his point.

"Good. Listen, I have someone stopping by for you. They'll be bringing some paper work and stuff for our next job. The plans, forms, stuff like that."

Michael frowned, going into his kitchen and pouring himself a whiskey. "You can't do that yourself? Or text me the details?"

Lester sniffled. "I'm feeling a little under the weather. Besides, I just hired O to the operation. The group, if you will. Helping me with the paperwork, information. Just overall helping. This'll be like, their first gig."

"Wait, what?" Michael started. The line went dead. "Dammit." He lowered his phone, almost tempted to call his nerdy friend back, but decided against it. He'd probably just get the voicemail. He sighed and finished his drink. Lester Crest was probably the most vague person he knew.

Why hadn't the dying genius told him that he was planning to bring another person into their circle? Now, instead of relaxing, like he had planned, he had to wait for some, _O_, to get to his place. He also didn't understand the vagueness of not using the persons real name, and just their first initial. O could be anything. Owen? No, that was too… pampered. Oscar? Sounded like some shamed gangster. Octavius? He gave up and poured himself another drink, only to have his door-bell ring moments later. O had arrived.

"Coming." Michael called, taking his time to get to the door, pulling it open. "Well its about time-" He blinked, staring at the person who stood on his front steps. This was definitely no Owen, Oscar, or, Octavius.

"Michael De Santa?" The young, brunette woman, asked, shyly, giving him a small smile.

Michael was lost for words. The appearance of the startlingly, attractive woman, had caught him completely off guard. "I…"

She smiled wider and held out her hand. "I'm Olivia Maxwell. Lester said he'd call you before I came."

Michael cleared his throat, trying to not look like such an idiot. "Oh, yah. Yah, he did. He said that you, O, would be coming. But I was under the impression that you were a-"

"Guy?" She laughed. "Yah, that's alright. You wouldn't really expect a woman in this type of business anyways. Though, sometimes, we can be the best at it." She gave him a playful wink. "May I come in?"

He nodded, "sure, sure. Come on in." He stood aside, giving her room to walk past him.

"Thanks." She gave him a smile and entered his house, looking around with an impressed gaze. "Your place is beautiful."

He shut the door, clearing his throat. "Thanks, cost me a fucking fortune. But it was definitely worth it. Pardon my french."

She turned her gaze to him with a laugh. "Language doesn't bother me, not to worry. You live in this big place by yourself?"

At that, Michael's face went pale, and he felt like he was grounded to the floor. "At the current moment…" His voice was weak. Ever since Amanda and the kids had left a few weeks ago, he'd been pretty damn alone. He hadn't even really talked to his family since they had left. Olivia nodded, thankfully not prodding him further into the subject. Michael, once again, cleared his throat. "Here, let's go talk in the kitchen." He led her into the spacious area and offered her a drink, which she thankfully took.

"So, I'm hoping Lester told you why it was _me_, he sent here, instead of meeting you somewhere himself?" She asked, taking a sip of her vodka and cranberry.

Michael nodded. "Yah, the prick said something about feeling under the weather or something. You're helping him out?"

She gave a short, dry, laugh. "In a way, I'm helping you all out. Sure, I'll be helping him with the paper work and all, but I'll also be joining you gentlemen on the heists, and shit like that."

He raised a brow. "So, how'd you get into business like this?" The second the words left his mouth, he regretted them. But Olivia merely shrugged.

"It pays. And _well_. The world is all about money, currently, Mr. De Santa. We all have a hunger for it. And the finer things."

He shrugged noncommittally. "Anyways… To the paperwork. What the hell do ya got for me?"

She put her drink down and reached into her bag, pulling out a folder. She placed it down on the counter before opening it up and pulling out a few papers. "This is all you need to know about the next mission. Crew, locations, pay, vehicles, all that jazz."

Michael took the papers from her and gave them a glance, snorting. "What the heck is 'Banks Exhumation'?"

Olivia had already taken back her file and put it away. "They're some meth dealers or something. I don't know. Lester didn't divulge in the details."

Michael raised his brows. "I thought you were supposed to know what the hell was happening."

She finished off her drink. "Banks Family. Big meth cartel here in Los Santos. One of their big daddy's just went bye-bye and they've just recently buried him. With a few treasures."

Michael nodded, impressed. "So, I'm guessing when it says, exhumation-"

Olivia nodded, "that's right. We're digging up the body, and taking all the expensive shit that was buried too. We're sinking down to the level of grave-robbers. My parents would be _so_ proud." She gave him a lopsided smile.

Michael chuckled, waving his hand assuredly, "if Lester told you anything about me, you'll know I've killed people. I can't sink any lower."

She winced slightly. "Yes. Lester did inform me that I would be working with gang members, robbers, psychos and murderers."

Michaels mouth went dry. "_Oh Jesus_. I didn't mean to scare you or anything… look-"

Olivia held up a hand to cut him off. "It's all okay. I knew what I was signing up for. Besides, Lester already filled me in on the characters of who I'd be working with. If I was so scared of you, being a murdering-robber and all, I wouldn't have come here period. Besides, for now, you seem pretty harmless."

He looked at her warily and finished off his drink. "Harmless eh?" His mind wandered to Franklin. Probably the most harmless out of their whole operation. "Well anyways… if you _do_ think I'm scary, wait till you meet Trevor."

She sipped her drink, laughing nervously. "Yes. Lester definitely warned me about that psyc- Mr. Philips. He said that he's the one I should be wary of, out of you three."

Michael nodded. "Franklin's practically a baby, and Trevor is the Hannibal-slash-Dhamer-Manson of our group."

Olivia raised a brow. "And you?"

Michael chuckled, opening his arms wide. "I'm a pretty open book, sweetheart. I'm in-between both of them, though, less psycho than T. And less innocent than F. I'm…"

"M?" She offered, smirking.

"Yes!" Michael said enthusiastically. He was on a roll. "I'm M! For Christ sakes. I'm the best out of them. The in-between guy!"

Olivia found herself laughing. She _had_ been nervous to come here at first, but now she felt rather comfortable around the middle-aged man, who's grey eyes had lit up with excitement and happiness. If truth be told, he looked like he needed it. "Well, M does sound like a good position to be in."

Michael nodded. "Like I said. It's the best fucking position there is."

Olivia started to come down from her laughter, glancing at the time on her phone. "_Shit_! I need to go. I still need to run by Franklin's, and I planned on getting to Trevor's before dark."

Michael raised his eyebrows. "All the way to Trevor's? Oh, that's a long _and_ far drive. I don't think you can make it before sundown. And you shouldn't drive out there on your own." He was more worried about her being alone with his psycho colleague-friend more than anything.

She waved her hand dismissively. "I can handle myself."

Michael shook his head. "No seriously, Olivia. Go make your call on Franklin, and I'll take you to Trevor's tomorrow. When the suns still up."

"_Really_?" She looked taken aback. "There's really no need."

"Really." Michael insisted. "Besides, we're _colleagues_ now. Its only the polite thing to do."

Olivia eyed him doubtfully before nodding. "Okay. _Alright_. I'll do my last call for the day, to Mr. Clinton, and then I'll call it a night. And tomorrow, come here…?"

"Where're you staying?" Michael asked quickly. "I'll come pick you up at nine."

She looked at him with sympathy and sighed. "The Marina. It's near the… Vanilla Unicorn." She winced.

"_No shit_?" Michael said, as if impressed. "I've stayed there a couple of times, after hanging at the Vanil…" His voice died off when he realized where he was going. Olivia gave him a questioning look, which made him cough. "Yah. I know where that is." He added, his voice suddenly serious and businesslike. _Good job, you fucking moron_, he cursed himself.

She nodded, gathering up her things. "Well alright then. I shall see you tomorrow, Mr. De Santa."

"Please," he said with a small smile, "call me Michael. We're all professionals here."

She snorted and nodded. "Alright."

Always being a gentleman, he walked her to her car, which was rather nice. Holding the door open for her, he flashed her a kind smile. "I shall see you tomorrow at nine, at The Marina. Drive safe."

Olivia gave him a small smile. "Thank you Mr. De- Michael. I'll see you then. And trust me. I always drive safe."

He watched her maker her way to the street, giving a small wave when she stopped before fully leaving the drive way. When she was out of sight, Michael headed back into his house. Back into the loneliness. He wentinto the kitchen, polished off her drink, and filled himself another of his. Then he went around and locked the doors, put his phone of charge, turned on the security, and went upstairs to sleep in his clothes. Before he drifted off he felt his smile linger as he had one last thought. _Must thank Lester tomorrow, for hiring O. _He then drifted off into a rather peaceful sleep.


	2. Chapter Two - Mr Philips

**Sorry to all who have been waiting for me to update again. Life has been crazy with school and exams. And I'm sorry for not having it on the days I said I would post it. . Don't shoot me please, lol. It is a day or two late, so not too big of a deal. Thank you to all who favorited/followed/reviewed. Your opinions are so important and make me work harder at getting this story out there. But anyways, without further ado, the long awaited chapter.**

**Disclaimer:**** As much as I would love to, I sadly, do not own the Grand Theft Auto franchise, or, any of the characters. I do, however, own my OC, Olivia, and any other OC's thrown into the story, along with the story line itself.**

* * *

**Chapter Two**

**_Mr. Philips_**

Michael pulled up outside of The Marina, ten minutes to the set meeting time. He glanced around him, making sure his rental car was clean. Ever since his shit-head son had stolen his real car, he had been stuck driving this shit rental. He sighed, eyeing the people that were coming and going from the hotel. It was a rather nice building; that much was for sure. In another moment, Olivia walked out of the front door dressed in classical Los Santos, summertime garments.

Short-shorts, tank top and her bag slung over her shoulder. Michael felt something stir inside of him and he bit down all thoughts that came into his mind. He just hoped to god that Trevor would show some decency. Michael gulped, opening his door and stepping out. Standing so that she could see where he was parked. She turned, smiling and throwing him a quick wave, which he returned.

"Hey stranger," she said as she approached with an enthusiastic smile.

"Hey O… Olivia."

She laughed lightly. "O, Olivia, Bitch. I go by all. Whichever you wish to call me."

Michael chuckled nervously, getting back into the car, "I'll probably end up calling you all of them at one point." He immediately wanted to slap himself. _You're such an idiot. You just told her you'd call her a bitch at some point. Brush up on your talking skills why don't you._

If he had offended her, she gave no notice, grinning broadly. "I'm somehow okay with that. Bitch was basically an endearment at my high school."

Michael started the car and began to exit the parking lot. "So, how was last nights meeting with the kid?"

"Oh, Mr. Clinton, or Franklin, was very kind. Very easy to talk to. He seems to rather look up to you, it seems. From the way he talks."

Michael puffed his chest a bit with pride, "yah, the kids kind of taken me on as a mentor."

Olivia laughed, "yes, he told me that. He also mentioned the story of how you too met. Your son's car repossession or something like that."

Michael chuckled, averting his eyes. Talking about his family lately always made him uncomfortable and sad. "Yah. It was something like that."

"Is he your only child?"

"What?" The question caught him off guard, and he glanced at her.

"Your son." Olivia's voice was calm and conversational. She didn't seem bothered by the fact that he hadn't brought up his family the previous night. Then again, neither had she.

"Oh, no. Jimmy's the oldest. My game-addicted-pot-smoking son. Tracey's the youngest. The princess TV-star wannabe."

Olivia chuckled, "I remember those days. Not too long ago. But you're very fortunate. To have a nice family and all. Are you married?" She immediate slapped her hand over her mouth. "God. This isn't any of my business. Sorry."

Michael shrugged indifferently, "it's no big deal. But yah. I am." He felt his wedding ring burn against his skin, as if branding him with the reminder. "But, uh, her and the kids… don't like my business endeavors. They took off somewhere."

"Oh…" Olivia looked down at her lap. "I'm sorry."

"Don't worry about it. My son stole some money and my car when he left. Shit-head. I'm sure they're alright."

She gave him a tender smile. "Teenagers. Always rebellious. But don't dwell on it. They're your family. They love you. They'll come back."

Michael shrugged, just wanting to get off the topic. "I'm hoping so… what about you?"

"My family?" She looked over at him.

"Yah." His eyes scanned ahead on the outstretch of highway, suddenly feeling embarrassed like she had before. "Unless… that's private."

"Oh, its okay." She shrugged, looking at the rocky scenery. "My dad's a business man… FIB." The car jerked, swerve so close to the edge of the road. "Are you trying to _kill _us?!"

"Your father works for the FIB?!" Michael's grip on the steering wheel was rather alarming, his visual contact with the road growing slimmer as he threw rapid shocked and angry glances at her.

Olivia rolled her eyes, her hand gripping the door handle. She somehow seemed unfazed by his reaction. "Lester knows, alright? We've deducted that it's a _good _thing. I can keep him- _them _off our trail." She looked at the way he was breathing, his grip on the wheel. "Will you relax? It's no big deal, trust me. We'll be okay."

He glanced at her, his breathing shallow, his eyes wide. His thoughts went to Dave and his manipulative nature. "You sure? Both of you?"

"Positive."

"Alright…" He relaxed considerably, but he still looked tense.

"Fuck. You would have thought I told you my father was the president. Relax, crazy."

Michael stared straight ahead, trying to calm his breathing. _She called you crazy._ Despite the situation he began to laugh. "Alright, alright, I'll relax… Now back to your story. Continue."

Olivia rolled her eyes, facing forward once more. "Anyways. My mom, now don't drive into the ditch, okay? She's a teacher."

Michael rolled his eyes. "Ha-ha, very funny."

They pulled up outside of the fence surrounding Trevor's trailer almost fifteen minutes later. Michael now knew a lot about O, thanks to the drive permitting them time to talk. Because of her parents' professions, she had lived a rather safe, secure, and by-the-book life. And she had just wanted out.

Michael could fully understand that. He had wanted out. And he had gotten out. Just to be fucking shoved right back in. He eyed Trevor's place, his heart sinking mercilessly. Anything that happened from here on out was inevitable and mostly out of their hands. He really just hoped that Trevor would be able to keep his cool and act semi-decent. They both climbed out of the rental car, opening the gate and walking to the front steps of the trailer, pausing outside the front door.

Michael gave Olivia a reassuring smile, feeling his gun in hidden in the back of his pants. "Just relax, O. Trevor is a ticking-time-bomb and a real wild-card. Try not to set him off. That'll be the worst thing we could both ask for."

Olivia gave him a calm smile, "don't worry, I'll behave."

Michael chuckled nervously. She wasn't the one he was worried about misbehaving. He gave the flimsy, aluminum door a good knock with his fist. Shouting rose up from inside the trailer, getting closer as the curser moved towards the door. Michael threw Olivia an apologetic glance just as the door flew open.

"RON! If its you, I swear to the statue of Impotent Rage that I will castrate your fucking- Michael! Buddy-boy, what are you doing here?"

Michael rolled his eyes, "just business T. All for Lester."

Trevor nodded faking his vehemence, his eyes going past his old friend, zeroing in on Olivia. "Ohoho, and who is _this _pretty little lady?"

Michael turned to introduce her, but Olivia stepped around him, nudging him out of the way and offering Trevor her hand. "Mr. Philips, I'm Olivia Maxwell. I'm joining this conundrum, helping Mr. Crest and all."

Trevor raised a brow, shaking her hand with a mischievous gleam in his eyes. "Well, this is a nice change of pace. I wont have to just look at these whores anymore."

Olivia gave him a smile, though Michael could see the falsity in it. He was relieved that Trevor wasn't picking up on her low comfort level. "Well," she continued, "I'm happy you think so. I'm very excited to be joining the team. I hope I am invaluable to you. But like Mr. De Santa said, we are here on business from Lester."

Trevor nodded, "well cutie, you an sugar-tits might as well come in then." He flattened himself against the door, giving the other two room to enter the trailer. He growled and slapped Michael on the ass as he walked buy, ending in him receiving a glare and the bird.

"Beer?" Trevor offered as he shut the door and joined the others in the rather wrecked and destroyed living room.

"None for me thanks." Michael said, taking a rather disgusted seat on the couch. "Its too early."

"Alright, suit yourself monkey-balls. And you, beautiful?"

Olivia shrugged, "why the hell not?"

"Perfect." Trevor excitedly bent down and pulled out two beers from the box on the floor, popping of the caps and handing her one. "Sohoho, what did that fat-dying-molester-freak send you two all the way out here for?"

Olivia sipped her beer, setting her bag down to retrieve her materials. "I apologize for intruding, but Lester wasn't really up for anything. He could barely get out of bed. I would've called but-"

"You wanted to see how fucking crazy I am?" Trevor's voice was deadpan, his features calm but cold.

"- Wanted to personally meet my fellow team player." She winced at his assumption, hoping he didn't truly believe. Sure, she had definitely been curious to see how crazy this Philips guy was, and he hadn't completely disappointed, but she had also wanted to meet him.

"Huh…" Trevor eyes her, licking his lips lightly, making Michael hang his head, "well, alright then, what's the next mission. Just give it to me fucking straight."

"A drug lords grave exhumation…?" She looked at him expectantly, waiting for a disgusted reply. He disappointed her.

"Woohoo!" Trevor's beer sloshed everywhere as he threw his hands in the air. "Fan-fucking-tastic. I've always wanted to be a grave robber. Yah baby!" He looked around the room, seeing the others' rather surprised and unenthusiastic expressions. "What? Some of us actually had childhood fantasies."

"Oh mother of god." Michael put his head in his hands.

"Yup," Olivia said with a grin, Trevor turning to her in confusion. "I was right to come here to see how crazy you are, because sir, you have lived up to my expectations."

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**So not really an exciting chapter, but I'm hoping you still liked it, and hopefully you think I wrote Trevor well. :) Let me know in a review. Remember to favourite, follow and review. :)**


	3. Authors Note

**Author's Note**

A quick authors note to my fabulous readers. Great news! I finished the game! So now I know hoe the game goes and will be able to fully write my story with no problems, being able to hopefully pump out the chapters quicker.

**_SPOILER ALERT_**: **For all who have not yet finished the game, do _not_ read the below/bold/boxed comment.**

**[For all who have finished and are wondering, yes, I chose Option C, because I love Trevor and Michael too much to part with either of them, and besides, the ending on Option C (and the song) were waaaaaay better than either of the other two options. Thankfully I knew that Option C would not be the demise of any of the trio, because I love Franklin too much (as well) to also sign him off on a death wish. I also watched the other ending on YouTube. Damn, T and M were killed in some bad ways. Obviously, Trevor's was more horrific, but still. And why would anyone _not_ want to play with all three after the games over?] **

With that said, (after fangirling a shit ton) a new chapter will be made and posted A.S.A.P. so don't fret, you won't have to wait too long.

I'm actually very happy, but also very sad that I finished the game because I was and still am very in love with it. But now I guess I can try something else, and free play the shit out of it.

Thanks again, and sorry to keep you all waiting. **Heart**

- Jane

**P.S. **You may have noticed my use of the shit word, ;) in this note. No, I am not against swearing, and in real-life, I have the seventeen-year-old girl mouth of a sailor, so no worries. If my language in my authors notes or story offends you, please look elsewhere. I will not change my speech, or my story. It's GTA after all people. What did you expect? ;)** And P.P.S. **Yes, T is my favourite character. I love the sexual, searing, sadistic, psycho that he is. Also so happy/proud that Steven Ogg (Trevor's voice and likeness) is from my home city.


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